Phenylboronic Acid → 6-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1,3-benzothiazole

HRID 2353366Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[F-].[K+].C1(P(C2C=CC=CC=2C2C=CC=CC=2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].C1COCC1>[CH3:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:3]([C:18]([F:21])([F:20])[F:19])[CH:4]=3)[S:9][C:10]=2[CH:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A microwave vial is charged with 2-(4-chloro-3-trifluoromethyl-phenyl)-6-methylbenzothiazole (170 mg, 0.519 mmol), phenylboronic acid (95 mg, 1.5 eq.), KF (90 mg, 3 eq.), Pd(OAc)2 (6 mg, 5 mol %), (dicyclohexylphosphino)biphenyl (18 mg, 10 mol %) and THF (0.5 mL). The mixture is heated to 120° C. for 30 minutes using microwave irradiation. The mixture is then filtered through celite and washed with EtOAc. The filtrate is concentrated and purified by column chromatography (EtOAc/Hexane, 5/95) to give 120 mg (63%) of 6-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)benzothiazole.

Workup

custommicrowave irradiation
filtrationThe mixture is then filtered through celite
washwashed with EtOAc
concentrationThe filtrate is concentrated
custompurified by column chromatography (EtOAc/Hexane, 5/95)

Sources & evidence

ORD record: ord-dbca517613394b319ceb441401d3aeff
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750021B2

Reaction notes

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